DE2331176A1 - Verfahren zur herstellung einer stickstoffhalogenamin-loesung - Google Patents
Verfahren zur herstellung einer stickstoffhalogenamin-loesungInfo
- Publication number
- DE2331176A1 DE2331176A1 DE2331176A DE2331176A DE2331176A1 DE 2331176 A1 DE2331176 A1 DE 2331176A1 DE 2331176 A DE2331176 A DE 2331176A DE 2331176 A DE2331176 A DE 2331176A DE 2331176 A1 DE2331176 A1 DE 2331176A1
- Authority
- DE
- Germany
- Prior art keywords
- solution
- nitrogen
- acid
- halogen
- amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000243 solution Substances 0.000 claims description 33
- -1 nitrogen halogen amine Chemical class 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 12
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 239000004471 Glycine Substances 0.000 claims description 6
- 208000002925 dental caries Diseases 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 238000005868 electrolysis reaction Methods 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229960003080 taurine Drugs 0.000 claims description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- OBRKOYNVXRUADL-BYPYZUCNSA-N (2s)-1-chloropyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1Cl OBRKOYNVXRUADL-BYPYZUCNSA-N 0.000 description 2
- DOSWGDLXZCTKIX-YFKPBYRVSA-N (2s)-2-(bromoamino)-4-methylpentanoic acid Chemical compound CC(C)C[C@H](NBr)C(O)=O DOSWGDLXZCTKIX-YFKPBYRVSA-N 0.000 description 2
- CUYRKZIJHCJEKT-YFKPBYRVSA-N (2s)-2-(iodoamino)-4-methylpentanoic acid Chemical compound CC(C)C[C@H](NI)C(O)=O CUYRKZIJHCJEKT-YFKPBYRVSA-N 0.000 description 2
- GMKMEZVLHJARHF-UHFFFAOYSA-N 2,6-diaminopimelic acid Chemical compound OC(=O)C(N)CCCC(N)C(O)=O GMKMEZVLHJARHF-UHFFFAOYSA-N 0.000 description 2
- FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 2
- 235000004554 glutamine Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 229910052701 rubidium Inorganic materials 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- FGBFBQULHKUDQV-IMJSIDKUSA-N (2r)-2-amino-3-[[(2r)-2-carboxy-2-(chloroamino)ethyl]disulfanyl]propanoic acid Chemical compound OC(=O)[C@@H](N)CSSC[C@H](NCl)C(O)=O FGBFBQULHKUDQV-IMJSIDKUSA-N 0.000 description 1
- DAOCALJTTFNUIY-BYPYZUCNSA-N (2s)-1-bromopyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1Br DAOCALJTTFNUIY-BYPYZUCNSA-N 0.000 description 1
- IRHTVZIUGVMYDI-BYPYZUCNSA-N (2s)-1-iodopyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1I IRHTVZIUGVMYDI-BYPYZUCNSA-N 0.000 description 1
- RLRYVSYUAHQYLS-QMMMGPOBSA-N (2s)-2-(bromoamino)-3-(4-hydroxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](NBr)CC1=CC=C(O)C=C1 RLRYVSYUAHQYLS-QMMMGPOBSA-N 0.000 description 1
- RPPLPTLNPSOPSB-REOHCLBHSA-N (2s)-2-(bromoamino)-3-hydroxypropanoic acid Chemical compound OC[C@H](NBr)C(O)=O RPPLPTLNPSOPSB-REOHCLBHSA-N 0.000 description 1
- ARNDBMMDZPKHMA-YFKPBYRVSA-N (2s)-2-(chloroamino)-3-(1h-imidazol-5-yl)propanoic acid Chemical compound OC(=O)[C@@H](NCl)CC1=CNC=N1 ARNDBMMDZPKHMA-YFKPBYRVSA-N 0.000 description 1
- BINIEVPVHDMWLB-JTQLQIEISA-N (2s)-2-(chloroamino)-3-(1h-indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(C[C@@H](C(=O)O)NCl)=CNC2=C1 BINIEVPVHDMWLB-JTQLQIEISA-N 0.000 description 1
- HKDIYFPRGVYHOI-QMMMGPOBSA-N (2s)-2-(chloroamino)-3-(4-hydroxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](NCl)CC1=CC=C(O)C=C1 HKDIYFPRGVYHOI-QMMMGPOBSA-N 0.000 description 1
- QRCAHEGWUXJKMU-REOHCLBHSA-N (2s)-2-(chloroamino)-3-hydroxypropanoic acid Chemical compound OC[C@H](NCl)C(O)=O QRCAHEGWUXJKMU-REOHCLBHSA-N 0.000 description 1
- YQYBDANXQKBAKJ-BYPYZUCNSA-N (2s)-2-(chloroamino)-3-methylbutanoic acid Chemical compound CC(C)[C@H](NCl)C(O)=O YQYBDANXQKBAKJ-BYPYZUCNSA-N 0.000 description 1
- ASVRUJBTDNHQMI-YFKPBYRVSA-N (2s)-2-(chloroamino)-4-methylpentanoic acid Chemical compound CC(C)C[C@H](NCl)C(O)=O ASVRUJBTDNHQMI-YFKPBYRVSA-N 0.000 description 1
- NZCZCNKLNYYFBC-BYPYZUCNSA-N (2s)-2-(chloroamino)-4-methylsulfanylbutanoic acid Chemical compound CSCC[C@H](NCl)C(O)=O NZCZCNKLNYYFBC-BYPYZUCNSA-N 0.000 description 1
- VMLMULDNFDPOMM-REOHCLBHSA-N (2s)-2-(chloroamino)butanedioic acid Chemical compound OC(=O)C[C@H](NCl)C(O)=O VMLMULDNFDPOMM-REOHCLBHSA-N 0.000 description 1
- OULUARVWFSHZJQ-VKHMYHEASA-N (2s)-2-(iodoamino)pentanedioic acid Chemical compound OC(=O)CC[C@H](NI)C(O)=O OULUARVWFSHZJQ-VKHMYHEASA-N 0.000 description 1
- CLKCODKAEWXAIQ-ZETCQYMHSA-N (2s)-2-(n-chloroanilino)propanoic acid Chemical compound OC(=O)[C@H](C)N(Cl)C1=CC=CC=C1 CLKCODKAEWXAIQ-ZETCQYMHSA-N 0.000 description 1
- JBFHLCLNUKCINB-REOHCLBHSA-N (2s)-3-hydroxy-2-(iodoamino)propanoic acid Chemical compound OC[C@H](NI)C(O)=O JBFHLCLNUKCINB-REOHCLBHSA-N 0.000 description 1
- GQAKENMGEKUHDM-VKHMYHEASA-N (2s)-5-amino-2-(bromoamino)-5-oxopentanoic acid Chemical compound NC(=O)CC[C@H](NBr)C(O)=O GQAKENMGEKUHDM-VKHMYHEASA-N 0.000 description 1
- WUNZCSWDOYZOPR-VKHMYHEASA-N (2s)-5-amino-2-(chloroamino)-5-oxopentanoic acid Chemical compound NC(=O)CC[C@H](NCl)C(O)=O WUNZCSWDOYZOPR-VKHMYHEASA-N 0.000 description 1
- WXLQWPLFENNGHA-BYPYZUCNSA-N (2s)-5-amino-2-(chloroamino)pentanoic acid Chemical compound NCCC[C@H](NCl)C(O)=O WXLQWPLFENNGHA-BYPYZUCNSA-N 0.000 description 1
- BSOXJTXLPLIVAG-YFKPBYRVSA-N (2s)-6-amino-2-(chloroamino)hexanoic acid Chemical compound NCCCC[C@H](NCl)C(O)=O BSOXJTXLPLIVAG-YFKPBYRVSA-N 0.000 description 1
- CPEGVQVQEKOVGU-GBXIJSLDSA-N (2s,3r)-2-(chloroamino)-3-hydroxybutanoic acid Chemical compound C[C@@H](O)[C@H](NCl)C(O)=O CPEGVQVQEKOVGU-GBXIJSLDSA-N 0.000 description 1
- QVJWPWBERRGLTN-WHFBIAKZSA-N (2s,3s)-2-(chloroamino)-3-methylpentanoic acid Chemical compound CC[C@H](C)[C@H](NCl)C(O)=O QVJWPWBERRGLTN-WHFBIAKZSA-N 0.000 description 1
- DLGAUVSRZXNATA-DHYYHALDSA-N (2s,3s)-2-amino-3-methylpentanoic acid;(2s)-pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1.CC[C@H](C)[C@H](N)C(O)=O DLGAUVSRZXNATA-DHYYHALDSA-N 0.000 description 1
- KHDXVKDLWMZLFM-DMTCNVIQSA-N (2s,4r)-1-chloro-4-hydroxypyrrolidine-2-carboxylic acid Chemical compound O[C@@H]1C[C@@H](C(O)=O)N(Cl)C1 KHDXVKDLWMZLFM-DMTCNVIQSA-N 0.000 description 1
- ZIRURAJAJIQZFG-UHFFFAOYSA-N 1-aminopropane-1-sulfonic acid Chemical compound CCC(N)S(O)(=O)=O ZIRURAJAJIQZFG-UHFFFAOYSA-N 0.000 description 1
- FEGLDXXHCNIVFP-UHFFFAOYSA-N 2-(bromoamino)acetic acid Chemical compound OC(=O)CNBr FEGLDXXHCNIVFP-UHFFFAOYSA-N 0.000 description 1
- USAWSWBIFACPGD-UHFFFAOYSA-N 2-(bromoamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNBr USAWSWBIFACPGD-UHFFFAOYSA-N 0.000 description 1
- XOLSHWCQPHGOPA-UHFFFAOYSA-N 2-(bromoamino)ethanol Chemical compound OCCNBr XOLSHWCQPHGOPA-UHFFFAOYSA-N 0.000 description 1
- JDWHRUJSFVABTL-UHFFFAOYSA-N 2-(chloroamino)-2-methylpropanoic acid Chemical compound ClNC(C)(C)C(O)=O JDWHRUJSFVABTL-UHFFFAOYSA-N 0.000 description 1
- BIECFEMCDBQPTL-UHFFFAOYSA-N 2-(chloroamino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NCl BIECFEMCDBQPTL-UHFFFAOYSA-N 0.000 description 1
- NMMHHSLZJLPMEG-UHFFFAOYSA-N 2-(chloroamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNCl NMMHHSLZJLPMEG-UHFFFAOYSA-N 0.000 description 1
- ZUUHDGNAOZSRRB-UHFFFAOYSA-N 2-(chloroamino)ethanol Chemical compound OCCNCl ZUUHDGNAOZSRRB-UHFFFAOYSA-N 0.000 description 1
- TYZYNGFWGHGRBZ-UHFFFAOYSA-N 2-(chloroamino)propanoic acid Chemical compound ClNC(C)C(O)=O TYZYNGFWGHGRBZ-UHFFFAOYSA-N 0.000 description 1
- YEDWGVWMZXICSQ-UHFFFAOYSA-N 2-(iodoamino)acetic acid Chemical compound OC(=O)CNI YEDWGVWMZXICSQ-UHFFFAOYSA-N 0.000 description 1
- XUGMGYUIGNYMJQ-UHFFFAOYSA-N 2-(iodoamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNI XUGMGYUIGNYMJQ-UHFFFAOYSA-N 0.000 description 1
- MNHBIAPEEQWPIZ-UHFFFAOYSA-N 2-(iodoamino)ethanol Chemical compound OCCNI MNHBIAPEEQWPIZ-UHFFFAOYSA-N 0.000 description 1
- QWCKQJZIFLGMSD-UHFFFAOYSA-N 2-Aminobutanoic acid Natural products CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 description 1
- ZVYADCOTSRZJFI-UHFFFAOYSA-N 2-[acetyl(bromo)amino]acetic acid Chemical compound CC(=O)N(Br)CC(O)=O ZVYADCOTSRZJFI-UHFFFAOYSA-N 0.000 description 1
- QGLFALHOWWFKJO-UHFFFAOYSA-N 2-[acetyl(chloro)amino]acetic acid Chemical compound CC(=O)N(Cl)CC(O)=O QGLFALHOWWFKJO-UHFFFAOYSA-N 0.000 description 1
- ZPGAQMYKMUKMOV-UHFFFAOYSA-N 2-[bromo(methyl)amino]acetic acid Chemical compound CN(Br)CC(O)=O ZPGAQMYKMUKMOV-UHFFFAOYSA-N 0.000 description 1
- VEXWJQOGAQWZGW-UHFFFAOYSA-N 2-[chloro(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(Cl)CCO VEXWJQOGAQWZGW-UHFFFAOYSA-N 0.000 description 1
- XALVEISOOLUDJW-UHFFFAOYSA-N 2-[chloro(methyl)amino]acetic acid Chemical compound CN(Cl)CC(O)=O XALVEISOOLUDJW-UHFFFAOYSA-N 0.000 description 1
- ZTWGZWADDCUMHM-UHFFFAOYSA-N 2-[iodo(methyl)amino]acetic acid Chemical compound CN(I)CC(O)=O ZTWGZWADDCUMHM-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 1
- PEMDAXJQNPLDAI-UHFFFAOYSA-N 3-(bromoamino)propanoic acid Chemical compound OC(=O)CCNBr PEMDAXJQNPLDAI-UHFFFAOYSA-N 0.000 description 1
- WJEBGQVOWZIZKS-UHFFFAOYSA-N 3-(chloroamino)propanoic acid Chemical compound OC(=O)CCNCl WJEBGQVOWZIZKS-UHFFFAOYSA-N 0.000 description 1
- CJKKUWQHHQMDJJ-UHFFFAOYSA-N 4-(chloroamino)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(NCl)C=C1 CJKKUWQHHQMDJJ-UHFFFAOYSA-N 0.000 description 1
- LUTIUIKEPTZAPP-UHFFFAOYSA-N 4-(chloroamino)benzoic acid Chemical compound OC(=O)C1=CC=C(NCl)C=C1 LUTIUIKEPTZAPP-UHFFFAOYSA-N 0.000 description 1
- OHVRSIILVXDJOG-UHFFFAOYSA-N 4-(chloroamino)butanoic acid Chemical compound OC(=O)CCCNCl OHVRSIILVXDJOG-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- UNMYWSMUMWPJLR-UHFFFAOYSA-L Calcium iodide Chemical compound [Ca+2].[I-].[I-] UNMYWSMUMWPJLR-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- QWCKQJZIFLGMSD-GSVOUGTGSA-N D-alpha-aminobutyric acid Chemical compound CC[C@@H](N)C(O)=O QWCKQJZIFLGMSD-GSVOUGTGSA-N 0.000 description 1
- LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 description 1
- 208000006558 Dental Calculus Diseases 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
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- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- 241000219995 Wisteria Species 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- OBESRABRARNZJB-UHFFFAOYSA-N aminomethanesulfonic acid Chemical compound NCS(O)(=O)=O OBESRABRARNZJB-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
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- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
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- 239000010439 graphite Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
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- QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
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- 229910052712 strontium Inorganic materials 0.000 description 1
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- 229910001631 strontium chloride Inorganic materials 0.000 description 1
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- 229910001643 strontium iodide Inorganic materials 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/27—Halogenation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Materials Engineering (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Metallurgy (AREA)
- Electrochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Dental Preparations (AREA)
- Indole Compounds (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3959172A GB1432549A (en) | 1972-08-24 | 1972-08-24 | Electrolytic method for the preparation of n-halo amino carbo xylic acids |
| US30088772A | 1972-10-26 | 1972-10-26 | |
| US30114272A | 1972-10-26 | 1972-10-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2331176A1 true DE2331176A1 (de) | 1974-03-07 |
Family
ID=27259573
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2331176A Pending DE2331176A1 (de) | 1972-08-24 | 1973-06-19 | Verfahren zur herstellung einer stickstoffhalogenamin-loesung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3776825A (enrdf_load_stackoverflow) |
| JP (1) | JPS5635752B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1007193A (enrdf_load_stackoverflow) |
| DE (1) | DE2331176A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2196800B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1432549A (enrdf_load_stackoverflow) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3921297A (en) * | 1974-10-15 | 1975-11-25 | Jaroslav Vit | Chemically active decay attacking liquid administering apparatus and fatigue relieving connection therefor |
| US4699589A (en) * | 1986-02-07 | 1987-10-13 | National Patent Dental Products, Inc. | Apparatus and method for supplying a heated liquid |
| JPH0720476B2 (ja) * | 1987-05-19 | 1995-03-08 | 松村 義男 | 口腔洗浄装置 |
| DE4041703C2 (de) * | 1990-12-24 | 1993-10-21 | Waldemar Dr Gottardi | Alkalimetallsalze des N-Chlortaurins in kristalliner Form, Verfahren zu deren Herstellung und deren Verwendung |
| JPH04273813A (ja) * | 1991-02-28 | 1992-09-30 | Kanebo Ltd | 口腔用組成物 |
| US7423064B2 (en) * | 2004-09-24 | 2008-09-09 | Olatec Industries, Llc | Composition for treating bacterial, viral, fungal diseases, inflammation and pain |
| US8747740B2 (en) * | 2007-01-25 | 2014-06-10 | Hercules Incorporated | Process and apparatus for generating haloamine biocide |
| US8956157B2 (en) * | 2012-01-31 | 2015-02-17 | Alexander Philippovich Rutberg | Apparatus and method for treatment of periodontal disease |
| US20140018432A1 (en) | 2012-07-12 | 2014-01-16 | Hercules Incorporated | Electrochemical generation of chlorinated urea derivatives |
| CA2968405C (en) | 2014-12-09 | 2022-08-09 | Johnson Matthey Public Limited Company | Methods for the direct electrolytic production of stable, high concentration aqueous halosulfamate or halosulfonamide solutions |
| EP3359708B1 (en) * | 2015-10-06 | 2022-06-29 | De Nora Holdings US, Inc. | Electrolytic production of halogen based disinfectant solutions from waters containing halides and ammonia |
| ES2907961T3 (es) * | 2016-06-09 | 2022-04-27 | De Nora Holdings Us Inc | Producción electrolítica de soluciones de cloramina orgánica |
| EP4543203A1 (en) * | 2022-06-27 | 2025-04-30 | Terra Vera Corporation | Nutrient and/or antimicrobial solutions |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3449225A (en) * | 1966-02-01 | 1969-06-10 | Monsanto Co | Electrolytic processes for preparing halogenated organic compounds |
-
1972
- 1972-08-24 GB GB3959172A patent/GB1432549A/en not_active Expired
- 1972-10-26 US US00301142A patent/US3776825A/en not_active Expired - Lifetime
-
1973
- 1973-06-12 CA CA173,864A patent/CA1007193A/en not_active Expired
- 1973-06-19 DE DE2331176A patent/DE2331176A1/de active Pending
- 1973-06-25 JP JP7159873A patent/JPS5635752B2/ja not_active Expired
- 1973-07-17 FR FR7326440A patent/FR2196800B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50105601A (enrdf_load_stackoverflow) | 1975-08-20 |
| CA1007193A (en) | 1977-03-22 |
| FR2196800B1 (enrdf_load_stackoverflow) | 1977-01-28 |
| GB1432549A (en) | 1976-04-22 |
| JPS5635752B2 (enrdf_load_stackoverflow) | 1981-08-19 |
| AU5740773A (en) | 1975-01-09 |
| FR2196800A1 (enrdf_load_stackoverflow) | 1974-03-22 |
| US3776825A (en) | 1973-12-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |